Tuesday Tuneup- #71
Why Most Contractors Stay Stuck
Happy Tuesday everyone!
Most contractors don’t actually own a business...
They own a job... with stress, overhead, and no real way out.
You’re probably wearing all the hats...
Selling the jobs... checking on crews... chasing payments... fixing mistakes...
And somehow still trying to “find time” to grow the business.
Sound familiar?
This is the trap nearly every contractor falls into...
You start out as the technician...
You’re good at the work... clients trust you... so you just keep grinding.
But over time, that grind becomes a prison.
You can’t take a real vacation...
You can’t walk away from the day-to-day...
And even if the money looks decent, you’re not actually free.
Here’s the truth most people won’t tell you:
Until you step out of the technician seat and into the CEO role... your business will never scale.
You’ll keep hitting the same ceilings...
You’ll hire people who don’t last
You’ll make decent money, but always feel behind
You’ll never have time to actually fix the root problems
You’ll burn out... or worse, start resenting the thing you built
So what’s the difference between a technician and a CEO?
Technician mindset:
“I’ll just do it myself... it’s easier that way.”
CEO mindset:
“How do I build a system so I never have to do this again?”
The CEO isn’t smarter than the technician...
They’ve just stopped trying to be the hero.
Instead of solving the same problem 100 times... they solve it once with a system.
Here are 5 steps you can take to get unstuck and start making the shift:
1. Track where your time is going
Spend 3 days writing down everything you do... hour by hour.
Chances are, 70 percent of your day is filled with $20 tasks...
When your time should be spent on $1,000 decisions.
2. Delegate one low-level task immediately
Find one thing you do daily or weekly that someone else could handle...
Whether it’s sending estimates, booking appointments, or chasing invoices...
Give it away. Trust someone else to do it... even if they’re only 80 percent as good.
3. Create one repeatable process
Take one thing you do all the time and document it in simple steps...
Whether it's how you onboard a new hire... how you follow up with leads... or how you close a deal...
Put it in writing. This becomes the foundation of your business systems.
4. Build a scoreboard
What gets measured gets managed.
Start tracking your team’s performance... sales... jobs in pipeline... gross margin...
It doesn’t have to be fancy. A simple spreadsheet works.
But if you can’t see it, you can’t fix it.
5. Make decisions based on who you want to be
Don’t ask, “What’s easiest right now?”
Ask, “What would the CEO version of me do in this moment?”
Would they jump on the roof to save a crew? Or hire, train, and lead from the front?
Every time you make a decision... you’re either building a business that works without you...
Or one that requires you to work harder just to keep it alive.
You can’t scale chaos.
You can’t sell a job that depends on you doing everything.
But when you make the shift... when you build systems, hire leaders, and start acting like a CEO...
You build a business that’s actually worth something.
Not just to a buyer... but to your future.
Until next time, Happy Selling!